Studies toward the total synthesis of (-)-kampanol A: An efficient construction of the ABCD ring system

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7937-7940

  Iwasaki, Katsuhiko ^a,b   Nakatani, Mari ^a   Inoue, Munenori ^a   Katoh, Tadashi ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Conjugate addition; Kampanol A; Phenylselenium mediated cyclization; Ras farnesyltransferase inhibitor

Indexed keywords

BROMOBENZENE; CARBENOID; KAMPANOL A; KETONE DERIVATIVE; PHENOL DERIVATIVE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; REAGENT; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; CYCLIZATION; DRUG SYNTHESIS; OPTICAL ROTATION; STACHYBOTRYS; STEREOCHEMISTRY;

EID: 0037190855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01859-2     Document Type: Article

References (38)

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2. 50 values of 13 μM and >100 μM, respectively (Ref. 1).
3. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
4. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
5. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
6. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
7. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
8. For recent excellent reviews on Ras farnesyltransferase as a novel cancer therapeutic target, see: (a) Nammi, S.; Lodagala, D. S. Acta Pharmacol. Sin. 2000, 21, 396-404; (b) End, D. W. Invest. New Drugs 1999, 17, 241-258; © Leonard, D. M.; Sebolt-Leopold, J. S. Drugs Future 1999, 24, 1099-1106; (d) Qian, Y.; Sebti, S. M.; Hamilton, A. D. Biopolymers 1997, 43, 25-41; (e) Sugita, K.; Ohtani, M. Curr. Pharm. Des. 1997, 3, 323-334; (f) Leonard, D. M. J. Med. Chem. 1997, 40, 2971-2990.
9. The absolute configuration of 1 has not been discussed in the literature (Ref. 1).
10. Recently, Jarvis et al. reported the isolation of structurally closely related antibiotic, memnobotrin A, from Memnoniella echinata organism, in which the γ-lactone ring (E ring) in 1 is only replaced by a γ-lactam ring, see: Hinkley S.F., Fettinger J.C., Dudley K., Jarvis B.B. J. Antibiot. 52:1999;988-997.
11. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
12. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
13. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
14. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
15. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
16. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
17. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
18. Synthetic studies including total synthesis of structurally analogous sesquiterpenoids, such as hongoquercins A and B, puupephenone and its analogues, and UPA0043 and UPA0044, have been reported. See for hongoquercins A and B: (a) Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297-302; (b) Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410-1415. See for puupephenone and its analogues: © Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391; (d) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208; (e) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Herrador, M. M.; Chahboun, R.; Galera, P. Bioorg. Med. Chem. Lett. 1999, 9, 2325-2328; (f) Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, B. Tetrahedron Lett. 1997, 38, 7249-7252; (g) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. See for UPA0043 and UPA0044: (h) Takao, K.; Sasaki, T.; Kozaki, T.; Yanagisawa, Y.; Tadano, K.; Kawashima, A.; Shinonaga, H. Org. Lett. 2001, 3, 4291-4294.
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21. While related conjugate addition reactions have been previously described in the literature, to our knowledge, the conjugate addition reaction between 10 and the Grignard reagent prepared from sterically hindered ortho-disubstituted bromobenzene derivative such as 14 is unprecedented, see: (a) Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084; (b) Mori, K.; Komatsu, M. Bull. Soc. Chim. Belg. 1986, 95, 771-781; © Welch, S. C.; Prakasa Rao, A. S. C. J. Org. Chem. 1978, 43, 1957-1961; (d) Welch, S. C.; Prakasa Rao, A. S. C. Tetrahedron Lett. 1977, 505-508; (e) Ireland, R. E.; Baldwin, S. W.; Welch, S. C. J. Am. Chem. Soc. 1973, 94, 2056-2066.
22. While related conjugate addition reactions have been previously described in the literature, to our knowledge, the conjugate addition reaction between 10 and the Grignard reagent prepared from sterically hindered ortho-disubstituted bromobenzene derivative such as 14 is unprecedented, see: (a) Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084; (b) Mori, K.; Komatsu, M. Bull. Soc. Chim. Belg. 1986, 95, 771-781; © Welch, S. C.; Prakasa Rao, A. S. C. J. Org. Chem. 1978, 43, 1957-1961; (d) Welch, S. C.; Prakasa Rao, A. S. C. Tetrahedron Lett. 1977, 505-508; (e) Ireland, R. E.; Baldwin, S. W.; Welch, S. C. J. Am. Chem. Soc. 1973, 94, 2056-2066.
23. While related conjugate addition reactions have been previously described in the literature, to our knowledge, the conjugate addition reaction between 10 and the Grignard reagent prepared from sterically hindered ortho-disubstituted bromobenzene derivative such as 14 is unprecedented, see: (a) Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084; (b) Mori, K.; Komatsu, M. Bull. Soc. Chim. Belg. 1986, 95, 771-781; © Welch, S. C.; Prakasa Rao, A. S. C. J. Org. Chem. 1978, 43, 1957-1961; (d) Welch, S. C.; Prakasa Rao, A. S. C. Tetrahedron Lett. 1977, 505-508; (e) Ireland, R. E.; Baldwin, S. W.; Welch, S. C. J. Am. Chem. Soc. 1973, 94, 2056-2066.
24. While related conjugate addition reactions have been previously described in the literature, to our knowledge, the conjugate addition reaction between 10 and the Grignard reagent prepared from sterically hindered ortho-disubstituted bromobenzene derivative such as 14 is unprecedented, see: (a) Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084; (b) Mori, K.; Komatsu, M. Bull. Soc. Chim. Belg. 1986, 95, 771-781; © Welch, S. C.; Prakasa Rao, A. S. C. J. Org. Chem. 1978, 43, 1957-1961; (d) Welch, S. C.; Prakasa Rao, A. S. C. Tetrahedron Lett. 1977, 505-508; (e) Ireland, R. E.; Baldwin, S. W.; Welch, S. C. J. Am. Chem. Soc. 1973, 94, 2056-2066.
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34. 2/-60°C→rt), the undesired C-7 epimer of 19 was exclusively produced in 86% yield. This stereochemical outcome can be rationalized by considering that the inner phenolic hydroxy group attacks the C-7 tertiary carbocation, in situ generated by acid treatment, from the less hindered α-face of the molecule under the influence of the β-oriented axial methyl group at the decalin junction.
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38. +).